Carbon Dioxide → 2,7-Dimethyl-9H-fluorene-9-carboxylic acid

HRID 1089845Notes

Reaction equation

HRID 1089845 reaction equation
[CH3:1][C:2]1[C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][C:12]=3[CH3:15])[CH2:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[C:21](=[O:23])=[O:22].O>C1COCC1>[CH3:15][C:12]1[CH:11]=[CH:10][C:9]2[C:5]3[C:6](=[CH:14][C:2]([CH3:1])=[CH:3][CH:4]=3)[CH:7]([C:21]([OH:23])=[O:22])[C:8]=2[CH:13]=1

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 962WaterHCID 143895334,5-Dimethyl-9H-fluoreneHCID 178418339Butyllithium

Product 1

HCID 3483962,7-Dimethyl-9H-fluorene-9-carboxylic acidYield 65.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4,5-dimethylfluorene (5.2 g, 27.0 mmol) in 100 mL of THF at -78° C. was charged with butyl lithium (18.7 mL, 29.0 mmol). The reaction mixture was stirred for 15 min, then CO2 gaseous (5 g, 113.6 mmol) was introduced via cannula over a period of 15 min at -78° C. The reaction mixture was warmed up to room temperature and stirred overnight. Water was added (150 mL) and the layers were separated, the water layer was washed with ethyl acetate (5×20 mL), then acidified with conc. HCl. The precipitate was collected, washed with water and dried to give 2,7-dimethyl-9-fluorenecarboxylic acid (4.24 g, 65.9 %).

Workup

  1. stirringstirred overnight
  2. customthe layers were separated
  3. washthe water layer was washed with ethyl acetate (5×20 mL)
  4. customThe precipitate was collected
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-054c463ad0a642bab4e00abd9dbe8f93
Source dataset
uspto-grants-1992_01
Patent number
US05079260

Reaction notes

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